N-(18-Hydroxylinolenoyl)-l-Glutamine

A Newly Discovered Analog of Volicitin in Manduca sexta and its Elicitor Activity in Plants

Naoko Yoshinaga, Chihiro Ishikawa, Irmgard H. Seidl-Adams, Elizabeth Bosak, Takako Aboshi, James Homer Tumlinson, III, Naoki Mori

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Plants attacked by insect herbivores release a blend of volatile organic compounds (VOCs) that serve as chemical cues for host location by parasitic wasps, natural enemies of the herbivores. Volicitin, N-(17-hydroxylinolenoyl)-l-glutamine, is one of the most active VOC elicitors found in herbivore regurgitants. Our previous study revealed that hydroxylation on the 17th position of the linolenic acid moiety of N-linolenoyl-l-glutamine increases by more than three times the elicitor activity in corn plants. Here, we identified N-(18-hydroxylinolenoyl)-l-glutamine (18OH-volicitin) from larval gut contents of tobacco hornworm (THW), Manduca sexta. Eggplant and tobacco, two solanaceous host plants of THW larvae, and corn, a non-host plant, responded differently to this new elicitor. Eggplant and tobacco seedlings emitted twice the amount of VOCs when 18OH-volicitin was applied to damaged leaf surfaces compared to N-linolenoyl-l-glutamine, while both these fatty acid amino acid conjugates (FACs) elicited a similar response in corn seedlings. In both solanaceous plants, there was no significant difference in the elicitor activity of 17OH- and 18OH-volicitin. Interestingly, other lepidopteran species that have 17OH-type volicitin also attack solanaceous plants. These data suggest that plants have developed herbivory-detection systems customized to their herbivorous enemies.

Original languageEnglish (US)
Pages (from-to)484-490
Number of pages7
JournalJournal of Chemical Ecology
Volume40
Issue number5
DOIs
StatePublished - Jan 1 2014

Fingerprint

Manduca
Manduca sexta
Glutamine
glutamine
Tobacco
Volatile Organic Compounds
Herbivory
volatile organic compounds
tobacco
herbivores
volatile organic compound
eggplants
herbivore
Solanum melongena
Zea mays
maize
Seedlings
Hydroxylation
seedling
alpha-Linolenic Acid

All Science Journal Classification (ASJC) codes

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry
  • Medicine(all)

Cite this

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title = "N-(18-Hydroxylinolenoyl)-l-Glutamine: A Newly Discovered Analog of Volicitin in Manduca sexta and its Elicitor Activity in Plants",
abstract = "Plants attacked by insect herbivores release a blend of volatile organic compounds (VOCs) that serve as chemical cues for host location by parasitic wasps, natural enemies of the herbivores. Volicitin, N-(17-hydroxylinolenoyl)-l-glutamine, is one of the most active VOC elicitors found in herbivore regurgitants. Our previous study revealed that hydroxylation on the 17th position of the linolenic acid moiety of N-linolenoyl-l-glutamine increases by more than three times the elicitor activity in corn plants. Here, we identified N-(18-hydroxylinolenoyl)-l-glutamine (18OH-volicitin) from larval gut contents of tobacco hornworm (THW), Manduca sexta. Eggplant and tobacco, two solanaceous host plants of THW larvae, and corn, a non-host plant, responded differently to this new elicitor. Eggplant and tobacco seedlings emitted twice the amount of VOCs when 18OH-volicitin was applied to damaged leaf surfaces compared to N-linolenoyl-l-glutamine, while both these fatty acid amino acid conjugates (FACs) elicited a similar response in corn seedlings. In both solanaceous plants, there was no significant difference in the elicitor activity of 17OH- and 18OH-volicitin. Interestingly, other lepidopteran species that have 17OH-type volicitin also attack solanaceous plants. These data suggest that plants have developed herbivory-detection systems customized to their herbivorous enemies.",
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N-(18-Hydroxylinolenoyl)-l-Glutamine : A Newly Discovered Analog of Volicitin in Manduca sexta and its Elicitor Activity in Plants. / Yoshinaga, Naoko; Ishikawa, Chihiro; Seidl-Adams, Irmgard H.; Bosak, Elizabeth; Aboshi, Takako; Tumlinson, III, James Homer; Mori, Naoki.

In: Journal of Chemical Ecology, Vol. 40, No. 5, 01.01.2014, p. 484-490.

Research output: Contribution to journalArticle

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AU - Yoshinaga, Naoko

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